Hollister
An older non-gated Windermere pocket with mature oaks and custom estates.
Live the MaxLife.
$1.1M
Median Price
$700K – $1.8M
130
Homes
$0–$60
Monthly HOA
1985
Established
Windermere Elementary
School Zone
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Background
A brief history
Hollister was platted in the mid-1980s on land that had been part of the original Windermere citrus holdings — one of the older non-gated residential areas that predates the gated-community wave of the 1990s and 2000s. Roughly 130 custom lots were released, most built out between 1985 and 2000 as one-off customs. The neighborhood's light governance (minimal HOA, no architectural review on most lots) is the reason Hollister reads as architecturally varied today — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, and a growing share of 2018+ farmhouse rebuilds share the same streets.
The feel
What it's like to live here
Hollister has the feel of an established Windermere neighborhood rather than a curated community — the kind of place where neighbors have lived for 20+ years and the tree canopy has grown in enough that summer afternoons stay cool under shade. Streets are lightly-trafficked two-lanes with no gate, no sidewalks on some blocks, and mature live-oak canopy throughout. Lots run 0.3 to 0.6 acre. The mix of long-tenured residents and newer renovation buyers gives the neighborhood a settled-but-refreshing character. Daily life orients around Windermere downtown (5 minutes) and the 429 for commute access.
The details
What to expect
Architecture & Lots
Architecturally mixed across four decades — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, 2018+ farmhouse rebuilds. Main homes 2,600–4,800 square feet. Lots 0.3 to 0.6 acre. Mature live-oak canopy throughout.
Lifestyle & Amenities
Non-gated, no community pool or clubhouse. The tree canopy and neighborhood quiet are the amenities. Residents walk or bike to Windermere downtown, Fort Gatlin Park, and the chain of city parks. Weekend farmers' market in downtown Windermere is a local institution.
HOA Rules & Fees
Annual HOA $0–$720 (some blocks have small HOAs for road and common-area maintenance; others have none at all). No architectural review. Short-term rentals technically permitted but uncommon. Low-restriction neighborhood — one of the reasons buyers choose Hollister over a gated community.
Schools
Zoned for Windermere Elementary, Gotha Middle, and Olympia High. Windermere Prep (private) is 4 minutes.
Access & Commute
Four minutes to Windermere downtown, 10 minutes to the 429, 15 minutes to Disney, 20 minutes to Restaurant Row, 30 minutes to MCO.
Community
Amenities
- Mature live-oak canopy throughout
- Four minutes to Windermere downtown
- Non-gated with minimal HOA governance
- Architecturally varied custom-build stock
- Lower entry point for Windermere school zoning
Know Before You Buy
HOA rules worth knowing
- Annual HOA $0–$720 depending on block
- No architectural review
- Short-term rentals permitted but uncommon
- Non-gated community
Education
School assignments
- Windermere Elementary
- Gotha Middle School
- Olympia High School
- Windermere Prep (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median trades in the $1M–$1.2M band. Unrenovated 1980s–1990s originals move $700K–$950K. Well-renovated homes run $1.1M–$1.5M. Recent custom rebuilds have closed $1.6M–$1.8M. Price-per-square-foot runs $250 for dated originals to $340 for renovated. Renovation status and lot size are the primary value drivers. Days-on-market has averaged 35–60 days.
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Homes available in Hollister
12 homes currently listed in Hollister.
$1,390,000
2014 Down Woods Ln
Windermere, FL 34786
4 bd · 4 ba · 3,344 sqft
Lake Down Woods
MLS# O6413750
$850,000
11155 Lake Butler Blvd
Windermere, FL 34786
3 bd · 2 ba · 1,935 sqft
Wauseon Ridge
MLS# O6414373
$2,999,000
5073 Latrobe Dr
Windermere, FL 34786
4 bd · 6 ba · 4,706 sqft
Isleworth
MLS# O6414325
$3,395 /mo
6873 Northwich Dr
Windermere, FL 34786
3 bd · 3 ba · 2,229 sqft
Lakes Windermere Ph 01 49 108
MLS# O6414222
$1,400 /mo
Windermere, FL 34786
1 bd · 1 ba · 528 sqft
Carrington Townhomes
MLS# O6414255
$14,990 /mo
801 W 2nd Ave
Windermere, FL 34786
5 bd · 7 ba · 5,639 sqft
Aladar On Lake Butler
MLS# O6414179
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 6, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA